Sodium Azide → 4-(Azidomethyl)-2,2-bis(trifluoromethyl)-1,3-dioxolane

HRID 1439524Notes

Reaction equation

HRID 1439524 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1([C:20]([F:23])([F:22])[F:21])[O:7][CH:6]([CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:5][O:4]1.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C)C=O.C1C=CC=CC=1>[F:1][C:2]([F:25])([F:24])[C:3]1([C:20]([F:23])([F:22])[F:21])[O:7][CH:6]([CH2:8][N:26]=[N+:27]=[N-:28])[CH2:5][O:4]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 21395816HCID 21395816, compound

Product 1

HCID 213958034-(Azidomethyl)-2,2-bis(trifluoromethyl)-1,3-dioxolane

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

A sample of 14.00 grams of 2,2-bis(trifluoromethyl)-4-tosyloxymethyl-1,3-dioxolane (m.p. 58°-60° C.) is dissolved in 40 ml of dimethylformamide and 4.85 grams NaN3 is added. The mixture is stirred magnetically at 140°-149° C. for 3.5 hours. The product is diluted with benzene and filtered. The filtrate is washed thoroughly with water, vacuum-stripped and distilled. The product, 2,2-bis(trifluoromethyl)-4-azidomethyl-1,3-dioxolane, has a boiling point of 78° C./20 mm Hg and a refractive index of 1.37447 at 20° C. Analysis Found: (In Percent) C, 26.95; H, 1.73; N, 16.06. Calculated for C6H5F6N3O2 (M.W. 265.1): C, 27.18; H, 1.90; N, 15.84.

Workup

  1. filtrationfiltered
  2. washThe filtrate is washed thoroughly with water
  3. distillationvacuum-stripped and distilled
  4. customat 20° C

Sources & evidence

ORD record
ord-5c566e98631c4829a51ab641ae970fde
Source dataset
uspto-grants-1977_11
Patent number
US04060532

Reaction notes

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